


Dark Fantasy

by FPwoper



Series: NaNoWriMo 2020 [22]
Category: Supernatural
Genre: (Including Misgendering to Female on Purpose), Air Restriction, Bottom Dean Winchester, Choking, Consensual Non-Consent, DEAN WINCHESTER IN PANTIES, Dean Winchester Has a Panty Kink, Dom Cain, Dom Castiel, Double Penetration, Feminization, Humiliation, Impact Play, Multi, Public Sex, Rape Fantasy, Risk Aware Consensual Kink (RACK), Slapping, Sub Dean Winchester, fantasies
Language: English
Status: Completed
Published: 2020-11-22
Updated: 2020-11-22
Packaged: 2021-03-10 07:49:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27669806
Author URL: https://archiveofourown.org/users/FPwoper/pseuds/FPwoper
Summary: Dean has had a fantasy for a long while, and he's finally shared it with Cas and Cain...SPN Kink bingo square: Double Penetration
Relationships: Cain/Castiel/Dean Winchester
Series: NaNoWriMo 2020 [22]
Series URL: https://archiveofourown.org/series/1995412
Kudos: 26
Collections: SPN Kink Bingo 2020





	Dark Fantasy

**Author's Note:**

> MIND THE TAGS!
> 
> This is prompt number 25 from my 30 NaNo 2020 prompts: Double Penetration + connoncon
> 
> This also fills the square "Double Penetration" for the SPN Kink Bingo 2020.
> 
> This work is unbeta'd.

When Dean initially told Cas and Cain about his long-hidden fantasy, they were appalled. Dean had sort of expected that, but seeing how open-minded his two partners, his _Doms_ , usually were, it did shock him. After Dean further explained why he wanted this, after he’d delved deeper into his own mind than ever, they reluctantly agreed but wanted to put their own spin on it. Cas and Cain discussed a few things amongst themselves, and Dean was eventually let in on their ideas, and he agreed immediately. He understood how they couldn’t exactly to this publicly, how both Cas and Cain were not comfortable with that, but playing at the club was a good substitute, and it would be a _safe_ location, too.

So Dean was excited for tonight, when they’d finally play out one of his oldest fantasies with two men he actually loved very much. Loving them was probably the one and only reason why he’d confided in them about this fantasy anyway. Dean prepared himself slowly and meticulously, opening himself up for the massive plug he’d be wearing. When he’d finally slipped it inside, he pulled on a dainty pair of panties that mostly consisted of lace, and then he pulled on an old pair of jeans and a snug t-shirt. Cas and Cain would be picking him up in an hour or so, because they had to make sure that the setting was ready and that the employees knew what was going to happen so no one would accidentally call the cops on them. Of course, their local BDSM club was used to a lot of different scenes, but informing them of any consensual non-consent scenes was in the contract they signed, and thus, his Doms had to inform management.

By the time Cas and Cain actually arrived, Dean was all hyped up again. He’d been looking forward to this scene for a few weeks now, and his anticipation was at an all-time high. Cas and Cain took their time kissing him before they helped him get into the car. Cain stayed with him on the back seat while Cas drove them over to the club. Dean was starting to become jittery with his nerves, and Cain’s touch was the only reason he wasn’t yet bouncing through the car. It grounded him before his nerves could actually eat him whole, and Cain was definitely aware of that. The older Dom had always had this soothing effect on Dean, and as Cas mostly enjoyed getting Dean riled up, the combination of the two men taking care of Dean worked like a miracle. He mostly scened with the both of them, but occasionally they split up, and Dean knew that Cas and Cain also got together sometimes, which he’d like to see someday. Now that they were actually dating, too, their playing had taken a backseat while they got to know each other better on a personal level. Tonight’s scene was the first in about a month, and Dean had an itch to scratch. He _needed_ to submit, or in this case, to be forced to submit to someone. He was so glad for Cas and Cain…

When they arrived at the club, Cain helped him get out of the car, still keeping close contact with him. “You remember what we agreed on?” Cain asked, and Dean nodded. “Can you repeat it for me once more?”

“Yes, sir,” Dean replied. “We’re going in and getting red bracelets so the people on the floor know we’re in an active scene, and they know not to interfere unless I safeword and you both ignore that.”  
“What’s your safeword?”

“Red, but if that can be interpreted as a general answer in the scene, it’s Impala.”

“Good, the staff are aware of your safewords too and will interfere if we do ignore it, but we will never do that to you.” Cain’s hand was still on Dean’s wrist, and Cas was joining him, trailing another hand down Dean’s other arm.

“And then?” Cas urged Dean to continue discussing the set-up of their scene.

“Then, we’ll break up for a little while and mingle on the play floor, until you both are ready. I will not know when exactly you will start enacting my fantasy.”

“Good, thank you for repeating that, Dean,” Cas said. With the lightest of pressure, Cas and Cain escorted Dean into the club, where they were greeted by someone from management who handed out the red bracelets they were to wear the entire night until they left or finished their scene. Dean didn’t get the chance to put it on himself, as Cas was already working on it.

Once their bracelets were on, Cas and Cain both kissed Dean’s cheek and waved at him. “Go mingle,” Cas said, “and we’ll find you in a little bit, okay?”

Dean nodded and smiled at them. The nerves that had mostly left his body were back again, but he forced himself to go look at a few of the scenes playing out in the open at the stages in the club. One pair in particular captured his eyes. A dark-haired man was tied to a breeding bench and he was being fingered to orgasm, if Dean was correct in his assessment of what the burly man behind him was doing. There was probably more to the scene, but Dean’s focus was mostly on the man on the bench, because his noises were so soft and beautiful. It was clear that the man had been edged for a while now because of the colour of his cock and how desperately he tried to move back on the other man’s fingers.

Dean knew he was technically also in a scene but couldn’t help but focus entirely on the scene in front of him because it was captivating. He was leaning against a wall just watching, and that was when Cas and Cain managed to surprise him. They were gentle but encircled his wrists and then pushed him face-first against the wall.

“Well, look what we’ve got here,” Cain said, leering at him.

Cas turned him around, pinning his wrists underneath his back. “Yeah, I get what you mean. It’s a pretty one indeed.”

“Shall we, then?”

Castiel simply nodded and caged Dean in, pinning his shoulders to the wall. “Don’t mind us.”

Instead of unbuttoning Dean’s jeans like he expected them to do, Cain took a hold of his jeans and _ripped_. There was enough force behind the movement that his jeans gave easily, and Dean gasped as the material fell from his body easily, without even taking his boots off.

“Oh Castiel,” Cain sighed, eyes wide and dark with lust. “Look at her, she’s wearing panties for us!”

Dean flushed and tried to hide his face, but Cas was still pinning him so he couldn’t move anywhere. He knew he was wearing the panties, of course, but he had no idea what other people’s reaction to them could be.

“I see, Cain,” Cas said, voice gravelly. “I think she was very much prepared for someone to see her pretty cock tonight.”

“What do you think, rip them off too? Or should we keep those on?” Cain was musing whether or not, although it seemed the decision was already made. Cas hummed and didn’t say anything. He just tore off Dean’s shirt too, and turned him around again, slamming Dean’s sensitive nipples into the hard brick of the club’s walls. It chafed and Dean moaned as pain and pleasure collided.

“I think she wants them off, based on the moan I just heard,” Castiel chuckled. Dean could feel eyes travelling over his back appreciatively, and he knew they’d garnered an audience by now. He had to suppress another moan at that.

“Castiel! I think she’s got another surprise for us!”

“Another one?” Cas asked. He was busy holding Dean’s wrists pinned to his lower back again, but it was clear he was also watching Dean’s ass and whatever Cain was doing there. Cain clearly had made a decision about the panty-tearing, as he tore the back of the panties open and tapped the plug Dean was wearing.

“Yes, Cas. She’s wearing a plug, so she’s all ready for us! We don’t even need to prep her or anything, and I think she can take the both of us at the same time in her tight little hole.”

“Do you think we can make her come without touching her cock at all, Cain?”

Cain laughed. “I think we can certainly try. If she won’t come on our cocks, she isn’t going to come at all.”

Dean whimpered at the veiled threat, but one of Cas’s hands came up to cover his mouth. “She does need to learn how to keep quiet, though. She’s very, very loud, and I don’t appreciate that right now.”

Dean swallowed and tried to remain a little more quiet. It was difficult to not moan or whimper as Cain slowly pulled out the plug he’d so carefully inserted an hour earlier, because the bumps and ridges were made to hit his prostate with every slight movement, and that is also what they did. Dean’s cock was straining against the front of his panties, which somehow were still on, even though the back of them was torn to hell. Maybe it was just his cock that made the panties stay up, who knew. Definitely not Dean.

“It’s definitely a big plug,” Cain said, “so we’ll just assume she can take both of us. Can I go first?”

“Maybe it’s easier if I go first – I can slip between her and the wall, and then you can slide in from her back. Might be easier, positioning-wise.”

Cain apparently nodded, because Cas pulled Dean from the wall and against his own body, positioning himself against the wall again. Then, he took his cock in hand and guided it towards Dean’s hole, pushing in quickly. Despite Dean prepping himself earlier, Cas pushing in so quickly stung a little, but it didn’t hurt too bad. Castiel somehow was still holding on to Dean’s wrists, which was a good thing, because as soon as Cain also started pushing in, Dean was struggling against the both of them. They’d never done this before, and it _hurt_ without additional lube, and Dean thought he was prepared enough for this, but he wasn’t.

“No, no, please stop,” Dean begged. “Please, it hurts, make it stop!”

Cain pulled out again and hit Dean’s ass. “Girls don’t get to ask if they want to be fucked by two cocks. They just have to be grateful that they are.” Instead of immediately sliding back in, though, Cain hit Dean’s ass a few more times, jolting Cas’s cock inside of him. He knew Cas loved seeing Dean get spanked, but apparently _feeling_ Dean get spanked is even better.

Eventually, Dean relaxed into the blows falling to his ass, and when he did, Cain pushed in again, this time ignoring Dean’s pained cry entirely. Castiel’s hand was quick to find Dean’s mouth again, pressing steadily against him to hush him again. Dean could barely breathe, but he felt more alive than he had in a while and the feeling of ecstasy was only mounting. Cain pushed in hard and fast and he was the one who set a quick rhythm, sliding out mostly before slamming back in again. Like they’d said, they didn’t care about Dean’s pleasure again – Cain’s hands were on Dean’s hips, Cas’s were on Dean’s mouth and one was still holding on to his wrists. No hands were near his cock whatsoever. They fucked him as quiet as he’d ever heard them – only occasionally moans and grunts filled the room around them, but there was no dirty talking whatsoever, and Dean felt grateful for that. He didn’t want to come yet, and dirty talking was a surefire way to get him to come in three seconds flat.

“Fuck,” Cas whispered a few minute into their rough fucking, as he came long and hard inside of Dean. Dean felt Cain’s hand take his wrists instead, and Cas moved his now-free hand towards Dean’s throat. “Are you going to come, too? Are you going to be a good girl for us and milk us?”

Dean wanted to nod but could barely move as it was. Cas didn’t care about the answer anyway, he _shouldn’t_ care about the answer anyway, and his fingers slowly pressed into Dean’s windpipe, cutting off his air supply. Dean gasped but couldn’t breathe in anymore, and he started struggling more and more against Cas and Cain. His brain was working frantically, but he couldn’t think clearly, and he was starting to panic a little when black spots started dancing in his vision and Cas let go again. Dean took in great gulps of air, but before he could get his breathing under control again, Cas slapped his face once, twice, three times, and Dean came hard, clenching down on Cas and Cain’s cocks. Cas gasped softly and shuddered, slipping out of Dean, and Dean actually felt Cain’s cock spurt out come as he grunted softly.

Cain slipped out as soon as he had come, and Dean felt soft hands trace over his back as Cas and Cain helped him sit down on the floor. Castiel pulled Dean further into an embrace, and Cain joined from the back. They were shielding him from those who were watching, which Dean appreciated a lot. The scene had seamlessly slipped into aftercare, and Dean was already feeling boneless and tired, but he was happy. It was less… unexpected than he’d maybe hoped for, but it was a good scene, and he probably had gotten it out of his system, wanting to be raped out on the street. This might not have been the street, but there were still many people watching who weren’t doing anything about Dean and his ‘aggressors’. He didn’t necessarily want them watching how he was comforted, though.

One of the people on the floor brought over a blanket, and Cain carefully wrapped Dean in it before he cuddled back up with Dean. Dean hadn’t even noticed that he was growing cold, and in the heat of the moment, he also hadn’t noticed that Cas and Cain hadn’t even taken any clothes off. They’d just fucked him with their jeans and shirts still on, which… fuck, that was hot. And Dean hadn’t noticed that tiny detail, something he’d told them he would enjoy if they’d incorporate it.

“Hey,” Cas whispered, pressing a soft kiss to Dean’s forehead. “How are you doing? Shall we get moving you to one of the aftercare rooms to clean you up and just cuddle?”

Dean nodded. “Doing good, very good, actually. I really enjoyed it. So many good new things that you came up with. I’m glad you didn’t tell me what exactly you were going to do, because it felt _real_ , now.”

“Good,” Cain said. “We’re going to move you to an aftercare room, then, and we can discuss this further while you drink a cup of hot chocolate and Cas and I take care of you further, okay?”

Dean tried to get his feet under him, but he was tired and apparently he was shaking, even, so it was difficult. He was glad for Cas and Cain’s hands, which were supporting him and helping him up, before the three of them moved to a special aftercare room. They had massive beds, couches, a small bathroom with a bathtub, and a full (but small) kitchen to prepare anything a sub might need after a scene. Dean preferred to lay in bed for a while with his Doms, but before he was going to sit down on the bed, he wanted to be cleaner than he was, come still leaking from his ass. He grimaced at the idea that he’d just left a trail of Cas and Cain’s come all over the floor leading to this room, and a puddle of come where he’d sat down on the floor, but it couldn’t be helped. He knew Cain loved seeing come leak from his ass, and Cas indulged him. Dean loved the feeling but hated cleaning it up, and so when Cas brought him a washcloth, he quickly cleaned himself up before planting himself squarely on the bed and inviting his partners up with him.

Cain quickly joined with a mug of hot chocolate for Dean, which Dean took gratefully. He sat down, leaning on Cain’s now bare chest as he slowly sipped his chocolate. Castiel joined them soon after, bringing a few snacks for them all to enjoy.

“So, you liked it?” Castiel said, lying down on Dean’s thighs.

“Yeah,” Dean said. “Your improvised details were very good. I… I uh, didn’t think I’d like the humiliation and feminization part that much, but it was strangely hot and got me in the right headspace, I guess.”

“You didn’t struggle as much as we were initially expecting,” Cain observed. “Did it still feel real enough for you?”

“Oh yeah.” Dean smiled broadly. “I’m not really one to struggle anyway, and if I’m honest… it didn’t feel right, because you’d be stronger anyway.”

“Was there anything you wish we’d have done differently?” Cas asked.

“God, I didn’t think we’d get to the performance review this quickly,” Dean joked, laughing now. “But no, I don’t think so. Maybe I should have been on the floor in the middle of the room or something, with just one of you initially, the other joining later, or… or instead of DP’ing me, you could have taken me one after the other? But those are things I think we could do later anyway, with slightly less planning, if that’s okay with you. I do love this setting, I like being… _feeling_ secure just before everything goes to hell for me.” Dean narrowed his eyes for a second before adding, “Look, what I liked less is that you ripped one of my favourite pairs of panties. I wasn’t quite prepared for that.”

Cain laughed, jolting Dean slightly. “Oh Dean, we’ll buy you new ones. I’m sorry for not preparing you for that, but I thought it was a nice touch.”

“It definitely was, thank you for that. Just… sad about the panties, I guess.”

“Well, if that’s all…” Castiel trailed off and kissed Dean. “Let’s just cuddle for a bit and then see how you’re doing in a bit before we head home again. I love you, you did so well tonight.”

“Thank you for being such a good boy, Dean,” Cain said. He kissed Dean’s shoulder and put an arm around his shoulder, pulling him back against himself. “Love you so much.”

“I love you too,” Dean said, sinking happily into Cain’s embrace. He was even happier when he felt Cas hug his backside, and it meant that he could settle and rest for a bit. Both of his partners were here, and they loved him so much that they just acted out Dean’s oldest fantasy, one that they didn’t particularly like themselves. But they did it for him, and Dean loved them so much for it.


End file.
